Sunset Cruise

Key West Private Sunset Charter

In Key West, we celebrate each and every sunset. Sure, we know another one is only 24 hours away, but each one is unique and beautiful. So we take a moment every day to appreciate the simple things, celebrate being alive in one of the most beautiful spots on earth, and toast the end of another day. It’s a quirky tradition that makes Key West a special place.

All About Your Key West Sunset Cruise

Why are sunsets such a big deal in Key West? Maybe it’s our location at the “end of the road.” Or maybe it’s just lucky geography—Key West is a fun East Coast port with an unobscured view of the western horizon. Or perhaps it’s because this island is a great place to catch a glimpse of the elusive Green Flash.

What’s the Green Flash, you ask? No, it’s not the latest Marvel superhero—it’s way better than that. The Green Flash occurs when just the right atmospheric conditions occur at sunset, and you have an unobscured view of the horizon. It only lasts a second or two, so look quick and stay sober! Or not. Either way, Key West is a great place to see it happen.

You may or may not see a Green Flash. And, of course, you can see the sunset with the crowd and street performers in Mallory Square—something everyone should do at least once. But seeing the sunset from the water on a private boat charter is a memorable experience—a relaxed and laid-back private show that will take you back to a quieter time on the island.

A few notes about Casual Mondays’ Key West sunset charters:
• Our charters leave from Oceans Edge Resort and Marina
• View the sunset from Key West Man-O-War Harbor
• Sights along the way include Sunset Key, Fort Zachary Taylor State Park (a Civil War fort), Key West Channel, and the Coast Guard and Navy bases.
• Interested in creating a custom sunset cruise package? Combine multiple activities into one charter boat trip (i.e., afternoon reef snorkeling + sunset, or Key West sandbar tour + sunset boat charter)
• We often see dolphins in the harbor, so remember your camera
• The exact route we take may change based on the wind direction
• All ages are welcome

Itinerary — Sunset Cruise, Key West FL

Sunset charters in Key West typically stick to Key West Harbor on the island’s western side. However, we leave from Stock Island on the East, so you’ll get an excellent tour of the island along the way.
• Leave the Marina
• Head out to Key West Harbor (about 20 mins)
• Cruise around the harbor for an hour or so
• Head back in (20 min)
• The entire trip ends up being around two hours long.

Captain Zak is a Keys history buff, so if you have any questions about Key West, her quirks, or characters, just ask. He’s a bastion of useless information that will help you win trivia night every time.

Booking your own private sunset cruise in Key West means you have complete control over the experience. If you’re thinking about also booking a snorkel or sandbar boat trip, let us know. We can create a custom trip for you and your group based precisely on how you want to spend your day.

We’ll pick where we go based on the weather that day. Your Captain will set a course for the best views and smoothest ride every time. For example, one of our favorite routes is to head south of the island and view the sunset from the Atlantic, so long as it isn’t rough out.

Here are Just a Few Things You Might See During a Sunset Cruise in Key West

• Dolphins, birds, wildlife, etc.
• Historic spots around Key West
• Incredible sunsets (voted the world’s best!)
• Learn about local history and Key West characters (Wreckers, Civil War, Spanish-American War, Henry Flagler, and his Overseas Railroad, Overseas Highway, etc.)

Pastel sunset sky glowing orange and pink over calm water with sailboat silhouettes anchored near Key West.

View from the deck of a boat looking out toward a golden sunset over calm ocean waters in Key West.

Vibrant orange and pink sunset over calm ocean waters with dark scattered clouds and distant island shorelines in Key West.

A smiling couple sitting on the bow of a boat enjoying a bright sunset over calm ocean waters in Key West.

Silhouetted sailboats and catamarans navigating open ocean waters under a vibrant orange Key West sunset.

A vibrant Key West sunset glowing orange and yellow over deep blue ocean water.

The bright orange sun setting directly on the calm horizon over dark, gentle ocean waves in Key West.

Low-angle view looking over the bow of a boat as the sun sets over calm ocean waters under a soft cloud-filled sky.

What To Bring On A Key West Private Sunset Charter

Here’s a list of a few items you’ll want to make sure you grab before setting off on your Key West sunset boat charter.

Hats
Beach towels
Sunscreen
Sunglasses
Sweater or jacket- it gets cooler after sunset
Cameras
Alcoholic Beverages (BYOB)
Food or snacks you might want for your trip
Your kids and fur-kids (Yes, we’re pet-friendly!)

What Not to Bring

Glass bottles
Spray-On Sunscreen

What’s Included When You Book a Luxury Sunset Cruise in Key West

What’s on the boat?
Here are a few items that Captain Zak keeps Still Dreamin’ stocked with.

• Beach Umbrella
• Pool noodles
• Football and other beach toys
• Ice
• Bottled water
• Bluetooth stereo
• Lifejackets, Safety equipment, and First Aid kit
• Blankets (In the winter months)
• Snorkels, Masks and Fins
• Paddleboards (Add-on)

About our Boat - Still Dreamin'

Still Dreamin’ is our flagship 32’ Belzona 325—an exceptional luxury center console that delivers the refinement of a yacht with the versatility of a performance vessel. Immaculately maintained and thoughtfully appointed, she offers a smooth, stable ride paired with true yacht-level comfort. From elegant bow lounging to seamless water access, every detail is designed to create a sophisticated, effortless day on the water in Key West.

Signature Features:

Expansive, plush wraparound seating with premium marine upholstery
Oversized bow sun lounger with integrated dining table
Spacious private head (bathroom) with fresh water shower
SureShade power awning for refined, on-demand shade
Dual sliding doors at water level for graceful water access
Premium sound system with crystal-clear audio
Open, walk-around layout for comfort and flow
Exceptionally smooth, quiet, and stable ride

A Note From Captain Zak

I think a sunset boat trip should be a daily tradition for everyone. There’s nothing like a sunset cruise in Key West, FL. There are many other islands and many other beach towns…but no other place has a sunset celebration so thoroughly ingrained in its culture as Key West.

The crowds on the square are fun and all, but nothing compares to taking your own sunset cruise tour. So hit me up, and let’s toast the sunset together because you can’t beat the view from out on the water.

Captain Zak

Toasting the Green Flash every night aboard the Casual Monday

If you are ready to experience the best Private Sunset Cruise that Key West has to offer, contact me, and we’ll set up the perfect itinerary.